Filing tells you what happened. Strategy changes what happens next.
By the time a return is prepared, every meaningful decision has already been made. Year-round advisory works on the decisions themselves: how income lands, when it lands, and what structure it lands in.
Built for complexity: equity compensation, K-1s, real estate, multi-state income. Timothy Simons, EA, MBA. Advisory engagements begin at $3,000 per year, fixed and in writing.
Not in the deductions list. In timing, structure, and elections.
RSUs, ISOs, and ESPP have decision points, not just tax bills
Vesting schedules, exercise timing, 83(b) elections where they apply, and withholding that almost never matches reality. Managed together, these decide whether a vesting year is painful or planned.
Pass-through income rewards people who plan for it
K-1 income brings estimated payment exposure, basis questions, and a qualified business income deduction with thresholds worth engineering around. It punishes the set-and-forget approach.
Real estate is a tax position, not just an asset
Passive activity rules, depreciation strategy, real estate professional status where the facts support it, and exclusion windows on a former residence that quietly expire. Timing is most of the game.
DC, Maryland, and Virginia treat you three different ways
The DMV is a three-jurisdiction puzzle by default. Add remote work, a relocation, or income sourced elsewhere and allocation stops being a formality. Getting it right is both compliance and strategy.
Three levels. The difference is how often we're in the room.
Every level runs on our ALIGN framework: assess the full picture, build the structure, then guide decisions all year. What changes is cadence and depth.
- Annual Finance & Tax Blueprint with the year's specific moves and deadlines
- Scheduled planning sessions plus preparation of the return the plan produced
- For one or two complexity factors and a year-by-year horizon
- Quarterly planning sessions and estimated payment management through the year
- Financial visibility reporting so decisions run on real numbers
- For stacking complexity: heavy equity comp years, K-1s, growing rental activity
- Monthly engagement and multi-year planning across every income stream
- Coordination with your attorney, financial planner, and insurance advisors
- For high income plus high complexity: liquidity events, portfolios, relocations
An initial plan. Then a full year of executing it.
Fit check
Five questions. It tells us whether strategy work would genuinely move the needle for you, or whether you just need a good preparer. We will tell you either way.
Diagnostic and blueprint
We review prior returns and your current-year picture, then build the blueprint: the specific moves, the deadlines they carry, and what each is worth.
Year-round execution
Planning sessions on your tier's cadence, estimated payments managed, and an open line before you make a money decision, not after. The return simply documents a year that was already planned.
One Advisor. The Same One, All Year.
Simonsgroup is a Washington, DC strategic tax advisory established in 2010, led by Timothy Simons, EA, MBA. Enrolled Agents are federally licensed in tax under Treasury Circular 230, and the boutique model means your plan is built and executed by the person whose name is on it, not handed down a staffing pyramid every spring.
Fixed annual fees, defined in writing before work begins.
Two minutes to find out if strategy work is worth it for you.
Five questions. Reviewed personally, reply within one business day. If the honest answer is that you don't need us, that's the answer you'll get. Prefer to talk? Call (202) 495-1404.
Asked by nearly everyone. Answered plainly.
I already have a CPA. Why would I need this?
Many clients keep their preparer. The gap is usually not preparation quality, it is that nobody is working the decisions between filings. If your current advisor calls you in March with ideas for the year that already ended, that is the gap.
Which level am I?
Cadence answers it. If your situation changes once a year, Strategy Partner. If it moves quarterly, Fractional CFO. If money decisions come up monthly and other advisors are involved, Private Office. The fit check plus a short discovery call sorts it out, and the final fee reflects your actual complexity, not the label.
Is this just for business owners?
No. A W-2 executive with heavy RSU vesting and a rental property often has more open planning questions than a small business does. Complexity, not employment type, is what determines whether strategy pays for itself.
When is the right time to start?
Before the decisions, which means now beats April by a wide margin. Most planning moves have deadlines during the tax year. Waiting until filing season converts strategy into archaeology.